(The Root) — Anyone black who's done time in prep school can appreciate the mixed bag of experiences it can bring: On the one hand, there's the potential — the promise — of receiving a world-class education, one that makes the transition to the Ivy League practically painless. On the other hand, there's the potential — the threat — of experiencing all kinds of feelings of alienation, the discomfort of being one of the "onlys," the kid everyone turns to stare at whenever the history teacher brings up slavery.

Such is the premise of American Promise, a two-hour-plus documentary debuting on Friday in New York theaters. (The film opens nationwide over the next few weeks.) When their precocious 5-year-old son, Idris, was accepted into the Dalton School — one of New York's most prestigious private schools — filmmakers Joe Brewster and Michele Stephenson, a middle-class black couple from Brooklyn, at first saw only promise.

"Dalton will open doors for him for the rest of his life," says Brewster, a trained psychiatrist. "Expecting great things," they turned the cameras on Idris and his best friend, Oluwaseun, or Seun, who was also accepted into Dalton. And they kept those cameras trained on the boys for the next 13 years. The result is a complex, though oft-times rambling, look at two black families trying to help their sons navigate a world of privilege, a world that often looks at them as the problem rather than the problem solver.

At first blush it would seem that the path of success for Idris and Seun would be relatively easy. They both hail from loving, two-parent, middle-class families (though Seun's family seems to be a rung or two down the economic ladder from Idris' family). They are both smart, funny, sweet. Dalton was in the midst of a concerted effort to bring in more students of color, and the boys were strong candidates.

But even in the allegedly postracial landscape of 21st-century America, race is never really post-anything. Stephenson worries what the boys will encounter going to school with "a bunch of rich white kids disconnected from the larger world," and as it turns out, she's right to worry.

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Seun's mother talks about when she discovered Seun in the bathroom, "trying to brush his teeth to get rid of the brown on his gums." Idris is suspended because he was accused of hitting another kid, an accusation he vehemently denies — and then he's suspended some more because the school thinks he's lying. Outside the school, on the playground in their more black neighborhood, Idris is teased for sounding white. "Sometimes I change my voice," he says, to fit in at home. At Dalton, he says, he never has to change his voice.

It's an age-old dilemma for any integration baby straddling two universes. And class and relative privilege don't seem to ameliorate that conflict very much at all.

The first half of the film does a good job of exploring that dynamic, following the boys everywhere, eavesdropping in on conversations in the family car, watching them in the classroom, on the playground, on the basketball court or in martial arts class. Idris seems to fit in easier than the dreadlocked Seun, but as the boys morph from cute kindergartners to pubescent middle schoolers, things get tougher for them, both academically and socially.

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It's heartbreaking to hear Idris talk about how he gets invited to so many of his classmates' bar and bat mitzvahs, but how he never gets to dance at them. The girls, he says, always turn him down. And yes, it makes him "feel bad."

"I don't know why they say no," he says softly. "I think if I was white, I'd be better off.

"Isn't that true?" he asks, staring into the camera. "At this school?"

Perhaps even more heartbreaking is watching these bright boys struggle academically. And as they struggle, the second half of the film shifts focus. The camera spends less time in the classroom at Dalton and more time in the filmmakers' Fort Greene home as they become increasingly frustrated with their son's school performance.

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The film's initial tone of cautious optimism ratchets up to one of mounting desperation. Idris' parents hire tutors, force him to study, berating him at times. And they meet with other black Dalton parents, who confess that they, too, are having trouble with their own black boys. One mother tells them her son entered Dalton "as an excellent student. And now he's going down."

"There's a cultural disconnect between African-American boys and the independent schools," says a Dalton official, adding that the African-American girls at Dalton don't have such problems.

Why? There are no easy answers, and the filmmakers seem to step away from answering the questions that they pose in the first half of the film, as if throwing up their hands in despair as well. As a result, the film seems to lose focus in the second half, meandering around as the boys make their way to high school. At times, Seun's story seems to be eclipsed by Idris' story.

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Still, despite its flaws, American Promise is worth a look. It's also a brave film. Brewster and Stephenson are willing to put themselves on blast, exposing the frayed nerves of parents who are often at their wit's end, frequently losing their tempers in their quest to do the best for the boy they love.

Teresa Wiltz is a journalist based in Washington, D.C.

Teresa Wiltz is senior staff writer at Stateline, the journalism outlet of the Pew Charitable Trusts.